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化学学报
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化学学报 ›› 2010, Vol. 68 ›› Issue (14): 1431-1436. 上一篇    下一篇

研究论文

(R)-苯并四咪唑催化的α-位带有官能团的苄醇类化合物的动力学拆分研究

陈沛然*，张怡，周辉，徐青   

  1. (东华大学化学化工与生物工程学院 上海 201620)
  • 投稿日期:2010-05-16 修回日期:2010-05-27 发布日期:2010-05-28
  • 通讯作者: 陈沛然 E-mail:prchensioc@hotmail.com
  • 基金资助:

    中央高校基本科研业务费专项资金

A Study on the Kinetic Resolution of Benzyl Alcohols Bearing Functional Group on α-Position Catalyzed by (R)-Benzotetramisole Catalyst

CHEN Pei-Ran, ZHANG Yi, ZHOU Hui, XU Qing   

  1. (College of Chemistry, Chemical Engineering and Biotechnology, Donghua University, Shanghai 201620)
  • Received:2010-05-16 Revised:2010-05-27 Published:2010-05-28
  • Contact: Peiran Chen E-mail:prchensioc@hotmail.com

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研究了(R)-苯并四咪唑催化的一系列α-位带有各种官能团的苄醇类化合物的拆分. 通过对反应结果的分析, 推导出此类底物拆分反应中存在的竞争性不对称诱导模型. 苯环与催化剂的cation-π相互作用和官能团π-体系与催化剂的相互作用会产生两种不同的、相互竞争的过渡态, 两种过渡态并存导致立体选择性降低及产物构型的改变.

关键词: 动力学拆分, 苄醇化合物, (R)-苯并四咪唑催化剂

Kinetic resolution of a series of benzyl alcohols bearing functional group on α-position catalyzed by (R)-benzotetramisole catalyst has been investigated. The competition between the cation-π interaction of the aryl ring of the substrates with the catalyst and the cation-π interaction of the functional group s π-system with the catalyst led to the decrease of the stereo-selectivity of the reaction and the configuration change of the products.

Key words: kinetic resolution, benzyl alcohols, (R)-benzotetramisole catalyst